This study aimed to evaluate changes in diet, adiposity, and metabolic outcomes after two years. In all, 358 Polish men aged 19–40 years old participated in the study. Data regarding dietary and lifestyle characteristics as well as family, socio-economic, and demographic status were collected using the food frequency questionnaire KomPAN®. Dietary lifestyle patterns were previously derived from data for 358 men by principal component analysis (PCA). Changes over time were examined in 95 men who returned after two years by calculating relative differences (RD, %) in mean values and markers distribution. Diet quality was described with two predefined scores: pro-Healthy-Diet-Index (pHDI) and non-Healthy-Diet-Index (nHDI). After two years, changes were observed in diet quality and metabolic health markers. No significant changes were observed in family, socio-economic, and demographic status, as well as other lifestyle factors. In the “sandwiches and convenience foods” pattern, an nHDI decrease (RD = −25.3%) was associated with a fasting blood glucose decrease (RD = −6.1%). In the “protein food, fried-food and recreational physical activity” and the “healthy diet, activity at work, former smoking” patterns, pHDI decreases (RD = −13.6% and −14.6%, respectively,) were associated with an adiposity increase. In the “fast foods and stimulants” pattern, no changes in pHDI and nHDI were observed, while adiposity markers and systolic blood pressure worsened. Conclusion: in the two-year perspective, dietary improvement was associated with improved glycemic control, despite no changes in body weight, while worsening of the diet quality or maintenance of unhealthy dietary behaviours were associated with the deterioration of metabolic health.